The COVID-19 pandemic has sped up digital health transformation across the health sectors to enable innovative health service delivery. Such transformation relies on competent managers with the capacity to lead and manage. However, the health system has not adopted a holistic approach in addressing the health management workforce development needs, with many hurdles to overcome. The objectives of this paper are to present the findings of a three-step approach in understanding the current hurdles in developing a health management workforce that can enable and maximize the benefits of digital health transformation, and to explore ways of overcoming such hurdles. A three-step, systematic approach was undertaken, including an Australian digital health policy documentary analysis, an Australian health service management postgraduate program analysis, and a scoping review of international literatures. The main findings of the three-step approach confirmed the strategies required in developing a digitally enabled health management workforce and efforts in enabling managers in leading and managing in the digital health space. With the ever-changing landscape of digital health, leading and managing in times of system transformation requires a holistic approach to develop the necessary health management workforce capabilities and system-wide capacity. The proposed framework, for overall health management workforce development in the digital health era, suggests that national collaboration is necessary to articulate a more coordinated, consistent, and coherent set of policy guidelines and the system, policy, educational, and professional organizational enablers that drive a digital health focused approach across all the healthcare sectors, in a coordinated and contextual manner.